The Best Laid Plans
by Fate Foretold
Summary: Notorious playboy Kol Mikaelson makes a bet with his best friend Jeremy Gilbert that he can sleep with the feisty Caroline Forbes before spring break. For this he devises a foolproof strategy that's sure to hand him the win. But things don't always go according to plan.
1. Chapter 1

Disclaimer: I don't own TVD, never did, never will.

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**The Best Laid Plans**

Of all the classrooms in all of the college campuses in the world, she had to walk into his.

She was a leggy blonde with charming baby blue eyes. She wore very little make up, just a bit of cheek blush here and some sleek lip gloss there, but the minimal maquillage fitted her just right because that way she radiated a look of innocence. Whether that look was real or not was something that commanded a different discussion.

She was really the perfect specimen: slender but toned arms, long slim legs, perfect pink lips. Dressed in a plain white shirt, a red cropped jacket, shorts and flats, she looked right out of a fashion look book. Her blonde hair was gathered into a side swept braid that fell perfectly in place on her shoulder. If Kol Mikaelson had even just an ounce of the poetic-ness that his older brother Klaus was full of, he would have said that she was beautiful.

But Kol wasn't Klaus, so he turned to Jeremy and whispered, "Look at that piece of ass."

Of all the things in the world that he could have said. But he couldn't take it back, so it lingered in the air and then Jeremy turned to him with an expression that was difficult to gauge.

Ah, Jeremy Gilbert. Nice, polite, boy next door Jeremy Gilbert. He'd been called almost everything from sidekick to moral compass, but Kol simply referred the term 'best friend' because that was honestly what Jeremy was, no matter how unbelievable it sounded.

What, you didn't think sharks could be best friends with angelfish?

"She's pretty," Jeremy said. "But you aren't you past the cheerleader phase? You could do better."

Kol probably could. Kol was, and not only according to his mother, a pretty good looking guy. Tall, confident, handsome. A conventional-handsome, homecoming king type. Ironically, he had been homecoming king. At their old school, a suburban bumblefuck for the privileged, he had really been something of a king. He made love to Anna the prom queen in the back of the BMW convertible that he borrowed from his dear brother Elijah (Oh if the man only knew what took place in his car, he would have, in all of his obsessive-compulsive glory, locked Kol in the ride and burned it down the ground). Then he dumped her the very next day and in the middle of a crowded hallway too. He was high-fived and the girls swooned. Everyone, really, hated the prom queen.

"What's wrong with the cheerleader? And dude, we don't even know that she's one." Kol said.

"She's just the type." Said Jeremy without further explanation.

Kol didn't argue because he himself knew that Ms. USA there was a cheerleader alright. He had fucked enough of them cheerleaders to know one when he saw one. "Well, what were you hoping to upgrade to in college? Law students?"

"I don't know, but don't you think you should try to take things a bit more seriously now?" Jeremy said with a finality.

Kol just shrugged. Fine, Jeremy wanted serious, let's show Mini Gilbert some serious.

He stood up and moved down the row, closing the distance between him and his leggy blonde beauty. She was alone but it seemed like she was waiting for someone because she put her bag on the seat on her left to her to save it. She then proceeded to take a pink notebook out and began to copy what looked like her class schedule into it.

He sat on her right. She didn't notice, or at least pretended not to.

"Hey," Kol said.

"Hi," she replied without looking up.

"What'cha doing?" he continued.

"Blind?"

Kol was surprised. Oh, this one was feisty.

"You know, there's a theory in psychology that says you can tell a person's attitude from his handwriting."

She didn't appear very interested. "Really."

"Yeah. See here, there's a slight curve at the end of the last letter in each word." Kol said, pointing at her penmanship. "It means you're that type of person who likes to play snobbish and out-of-your-league and what not, but you'll take a good time when you can get it."

"Wow. So can I suck your dick now?"

He was taken aback, not expecting that answer. "What?"

"Well, that's how most of these things go, right?" She said, finally looking up, "Small talk, blowjob. Sometimes in reverse. That's what you're used to, isn't it?"

"Hardly. Why? Is it like that for you?"

She rolled her eyes. She looked so pretty rolling her eyes.

And then the obligatory sidekick friend approached.

She was an olive-skinned brunette who was slightly shorter and about as slender as Barbie, with rich lips and interesting amber eyes that would have actually looked pretty if they didn't have that dark, angry, alarming, disarming look in them. She gave off an impression of strength – the determined, dangerous type that had a hint of irresistibility in it.

As Kol looked up at her, he decided that she was actually quite beautiful herself. Except that this girl seemed like she was a walking example of understatement. Honestly, she didn't look like she even took time to fix herself up. In contrast to Ms. USA who was at least a bit dolled up, this one didn't even bother to trouble with the blush and the lip gloss. She wore a simple printed shirt, dark jeans and ankle boots. No lush wavy feathery hair because her silky black hair was swept up in a plain ponytail that wasn't really the hairstyle to wear for anyone who wanted to flirt or at least get attention.

"Hey, Caroline," the other girl said. Caroline looked relieved at the brunette's arrival and retrieved her things from the chair she saved so that her friend could sit on it.

"Caroline? Hey Caroline," Kol said to the pretty blonde.

The obligatory friend raised her eyebrow and smiled in a strange sly way.

"Bye, dick." Caroline waved her fingers.

"Actually it's Kol."

He smiled at her and walked slowly away, his hands in his pockets.

When he reached his seat, Jeremy was staring at him with a grin on his face which annoyed the hell out of Kol.

"Shot. Down." Jeremy emoted triumphantly.

Huh. So much for best friend. Okay from now on Kol was going with 'sidekick'.

"Shut up," Kol replied kind of defeatedly and sat in his chair. Jeremy refused to stop the glistening grin.

"It's all right," Jeremy consoled sarcastically. "Even the great Kol Mikaelson has to be shot down sometimes, huh?."

"You know, man, if I remember correctly, I just told you to shut up."

"You memory must be a little fuzzy after the beat down you just received."

A beat down. It was, after all, a game, and thinking of it that way made Kol feel better. The thought stuck in his head for the remainder of the class, a boring lecture on Beowulf or Roland or someone else along those lines. Lord, tell him again why he even allowed Jeremy to talk him into taking this goddamn Literature elective because there was no way that he was going to attend this for a whole semester without going bananas.

Aenid, Iliad, Gilgamesh, it all seemed the same to Kol. He scoffed at literature - it was pointless. All that mattered in the world, he thought, was numbers. And what people thought of you. That was his father's philosophy.

His father was an old blood Republican. English roots, but his ancestors settled in the American South three centuries or something like that ago and entrenched themselves deep in the land. Now the Mikaelson patriarch the governor of Virginia. A lawyer by profession, a family man by choice. Or at least that's how his campaign painted him to be.

He wanted his youngest son to go to Yale, just like all of Kol's three older brothers: Elijah who collected big shiny academic medals that Kol had taken the liberty of hanging on the Christmas tree four years ago, Finn who spent half of his time winning chess Olympiads and the other half convincing his father to let him marry his red-headed tramp girlfriend, and Klaus who actually had to be gagged and dragged each and every single day to even get to the gates of Yale.

However, Senator Mikaelson's connections unfortunately could only guarantee Columbia for Kol's accomplishments. GPA: 2.35-SAT: 2360, but Kol never told his friends that, except Jeremy. It was just another part of an inexplicable life. He bragged about getting 1650. After all, he had a heavy hangover on the morning of the test. Maybe it was just a lucky accident. He took the test again. He entirely fumbled the last section. 2070. On the third try, he forgot his calculator at home. 2340.

He recalled comically all the teenagers in the world who would kill for his score. He would gladly trade places with them. His greatest fear in the world was making his father proud, lest the respectable senator turn him into what he had turned Kol's brother's into – boring lawyers groomed to follow their father's footsteps in public office. Hm, maybe the old Mikaelson was secretly working for the British forces and was in a mission to conquer America. In that case maybe Kol could reconsider.

When he was back in his dorm room, invested in a video game while Jeremy did homework, a thought came to him.

"She's too proud," he said.

Jeremy looked up from his work and turned to Kol.

"What?"

"That Caroline chick. She's too proud."

"Really, Kol, I don't want to ask."

"Look, the reason why she was such a bitch is that she's never had to be nice. Things just fall into her lap since she's so hot."

"I didn't ask."

"You have to treat queens like whores, Jeremy. Look at what happened to Anna."

Jeremy's face tensed for a second and then relaxed again. "Thanks for the bit of wisdom but I would really be more grateful if we start doing homework because we've got a fifteen page essay due tomorrow."

"I'll get her. You'll see."

"Right-well while you're at it, would you look into Nibelungenlied? We're supposed to make an exposition on the betrayal of Siegfried and its relevance to contemporary politics."

"Sure, I'll put it on my to-do list. Between white water rafting and flossing and-you know-"

"Impregnating Mila Kunis?"

"Oh!" he gasped, "Gotta add that. After I'm done with Caroline."

Jeremy sighed. "You really want to talk about Caroline? Fine. Listen, Kol, I'm telling you that you have a better chance with Mila Kunis than this Caroline girl. She's totally blew you off."

"She did not."

"She did, Kol."

"Tell you what. I'll bet you five hundred bucks that I'll get her."

"I don't need your money."

"Well, maybe not. What do you want?"

"For you to stop chasing after girls and maybe actually take college seriously?"

"Okay, fine. I bet you that I'll plow her before spring break. And if I don't you may convert me to Jeremy-ism."

Jeremy took a moment to consider. "Fine. But she has to be sober."

Kol grinned. "You underestimate me, my friend."

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A.N.: So I'm really a big Klaroline fan but these past few weeks I've been reading amazing Kolarolines here and in tumblr and it's impossible not to love this pairing because both Kol and Caroline are super adorable! I decided to try writing this ship as well.

If you liked it please review and tell me so I know whether I should continue this or not.


	2. Chapter 2

Disclaimer: Seeing that Kolaroline still isn't canon, it should be obvious that I don't own TVD.

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**The Best Laid Plans**

Sixty seven.

It was the exact number of girls that Kol had dated (where date equals fuck) in his entire four years in high school. Of this number, sixty seven were gorgeous like Caroline, thirty six were cheerleaders like Caroline, twenty five were blonde like Caroline and nine had told him to get lost the second he breathed the same air they did, just like Caroline.

He had dated enough girls like her and needless to say Kol had her all figured out. He might as well chop his own balls off if he gave her flowers or whatever other romantic crap. She was used to being chased and Kol had never been a beg-and-grovel kind of guy to begin with.

What gorgeous girls like Caroline were NOT used to was being ignored. And if Kol wanted to get Caroline's attention, then that was exactly what he needed to do.

The problem was, unless he was in close proximity to her, she would never even notice that he was ignoring her. He needed to get close _and_ get noticed but he needed to do both without paying Caroline any attention.

Which was even more complicated than it already sounded.

"Hey, have you figured out problem number four?" Jeremy suddenly asked, snapping Kol back into reality. The two of them were in one of the on-campus cafes on a lazy Wednesday afternoon trying to solve their Calculus homework – well actually only one of them was still trying to solve it.

Kol handed his friend his work sheet.

"You're done with _everything_?" Mini Gilbert gasped, almost choking at his mango-carrot blend.

Kol shrugged as he took a sip of his iced latte. Like all the problems that occasionally sprouted in his just-a-little-less-than perfect life, he was sure that a solution to his problem with Caroline would magically pop out of nowhere so he didn't need to sweat it. He got into Columbia with a 2.35 GPA for crying out loud, getting Caroline can't be so much harder than that.

And as if heaven was backing him all the way up, the door chimes sounded as the solution to Kol's problems entered the cafe and slipped behind the counter in three strides.

It was Caroline's obligatory sidekick friend. Apparently she worked there.

Kol grinned to himself before patting Jeremy on the back and telling him that he was going to buy a muffin. He walked towards the counter wearing a very bright smile.

"Hi, what would you like to -" the girl began. She dropped the obviously fake chirpy voice when she recognized him. "Oh. It's you."

"I'm flattered that you remembered." Kol replied, trying to sound as friendly as possible.

"Of course. It's kind of hard to forget that look on your face when Caroline shot you down, you know. Has anyone ever told you that you look like a sooky koala?"

"Yes, some antisocial bitch just told me. I don't think the antisocial bitch's boss would appreciate his employees calling precious paying customers sooky koalas, would he?"

She glared at him. "What do you want?"

"Right now? Gee, a Ferrari Berlinetta would be nice. So would a weekend in a Vegas strip club. But given that those two aren't among the options, I'll settle for your name."

"What?"

"Your name." Kol repeated. "What's your name?"

The girl pursed her lips and hesitated for a moment. Then she gave up and sighed.

"Bonnie. Bonnie Bennett."

Kol smiled smugly. "See, we're doing so much better already. Hello, Bonnie, I'm Kol Mikaelson. So listen, I kinda need –"

"Wait, Mikaelson?"

"Mikaelson. Moving on, I -"

"As in you're related to Governor Mikael Mikaelson?"

"Yes, he contributed the Y chromosomes that led to the creation of the glorious specimen in front of you, are you satisfied now? So, as I was saying –"

She folded her arms and huffed. "Oh, so Governor Mikaelson's son is here. Is that why Columbia's getting a new lecture hall next year?"

"Do you have a problem with lecture halls?" Kol replied coolly.

"No. But I have a problem with the fact that I busted my back in high school so I could get into this university and now I have to bust my back to afford to stay in it. And you," she said, glaring at him even harder. "You just waltz your way into Columbia because your dad is donating a pretty new building! Why is life so unfair?"

Kol suppressed the urge to snort. Fine, so the solution to the problem of how he would get into Columbia with his horrendous GPA wasn't really as magical as his father's bank account. But hey, it's not his fault if he happened to be born into a ridiculously loaded family, and if his governor of a father wanted to take politics beyond the government, then Kol certainly didn't have a problem with that.

"Wow, Bonnie, I feel so bad for you." he answered sarcastically, still smiling.

"Save it, jackass. I don't want your pity and I don't need it."

"Is your pillow talk always this charming?"

"If you're not going to buy anything, get out of my face."

"Relax, I intend to buy something, alright."

"What do you want?"

Finally, Kol thought. It was really getting hard to play nice with the bitch. "I need you to help me get Caroline."

She rolled her eyes. "Is that a joke? Where's the punch line, buddy?"

"I'm not kidding. I want Caroline, and I need you to help me get her."

Bonnie was quiet for a moment. And then she burst out laughing. "You want Caroline and you want me to help you get it on with her?"

"I have a few other particular things in mind, but you get the general idea."

"Yeah, right. Like I would ever help some spoiled douchebag come onto my room mate."

"Chill out, Bon-Bon. I told you that I intend to buy something, right? Well I'm not asking you to help me as a favor. I'll pay you."

She took some cloth and began wiping the counter. "You know what, take your money and shove it up your ass. Just because you bought your way into Columbia doesn't mean you can buy your way into everything else."

"Here's a hint, sweat pea. The only people who say that money can't buy everything are the people who never had any."

"Go away, Mikaelson. Jump off a cliff and rid the world of another fucktard."

"Kaching, kaching, did I hear you say 'how much'?"

"No, you heard me say 'Go fuck yourself'."

"One thousand dollars."

She stopped wiping.

"What's that, do I finally have somebody's attention?" Kol teased.

She almost flung the rag cloth into his face. "You're an ass."

"Fair enough, but I'm an ass with a thousand dollars and that's more than what I can say about you."

She didn't answer.

"Come on, Bon-Bon. Think about all the books and all the readings that you're going to need this semester. They're going to cost a lot, and you're cleaning counters right here."

Bonnie hesitated. She wasn't rich, but she prided herself in having dignity and integrity, and if it was all up to her she would have done the right thing to do at that moment - walk up to Kol Mikaelson and bitch slap the jerk in the face.

But the truth was that she could use an extra thousand dollars. She got into Columbia with 30% of her tuition being shouldered by a merit grant, but what was left of the $50,000 school fees, plus the books, boarding, and the general cost of living in New York still presented a hefty sum to pay. And at the end of the day she didn't want her father to spend every penny he made on her because he deserved a comfortable nest egg when he retired, especially with her mom out of the picture. Wasn't that why she decided to get this crappy cafe job in the first place?

"How much do they pay you for this job? Nine dollars an -"

"Shut up." Bonnie said. Her voice sounded strained.

Kol stared at her expectantly, the cocky smile still plastered on his face.

She swallowed. This was Caroline, her friend, that they were talking about. She couldn't – shouldn't – feed her to the lions just like that! But on the other hand, they were also talking about one thousand dollars. How many people were paid one thousand dollars to play bridge between some rich (but admittedly handsome) spoiled brat and the pretty girl he wanted?

Bonnie bit her lip as she felt her resolve mellow. Maybe Kol just liked Caroline. Maybe the bastard just liked her so much that he would do anything to go out with her. Maybe he just really, really liked Caroline. And if that was the case, then why not? Who knows, maybe some of Caroline's niceness would rub off that arrogant jerk if they dated.

Finally, she took a deep breath. "You have to pay me upfront. In cash."

He smirked. "You'll be paid when I get Caroline."

"Upfront." she said firmly.

He shrugged and reached for his wallet. Bonnie felt ashamed as she watched him pull out a couple of bills and placed them on the counter in front of her.

"Half now, half when I get Caroline."

Kol winked at her and walked back to his table.

Bonnie looked at the money on the counter. She felt awful selling Caroline out like that, honestly. Even though they'd known each other for only a while, being room mates during their first year in Columbia, Caroline had been nothing but a good friend to her. Still, one thousand dollars was one thousand dollars. Dignity and integrity didn't pay for books and board. Dollars did.

Glancing at her boss to make sure that he wasn't looking at her, Bonnie took the money and hurriedly slipped it into her pocket.

"Took you long enough." Jeremy said when Kol came back. "Where's your muffin?"

Kol looked down on his empty hands. The muffin, right. He totally forgot.

Jeremy glanced at the counter and saw Bonnie, who had began rearranging the tray of brownies on display. He turned to look back at Kol with an incredulous expression.

"Okay, please don't tell me you left me to flirt with that girl."

"What? No."

"Seriously, Kol. She looks like she's a decent person who doesn't deserve to be dragged down to tell with you."

"Chill, dude. She's yours if you want her. If I'm going to flirt with anyone, it's going to be with Caroline. The bet is on, remember?"

Jeremy shrugged. The bet was on, right. If Kol didn't get into Caroline's panties before spring break, he'd lay low on the doucherbaggery and maybe actually do some studying in college. If Caroline did give in to Kol, Jeremy had to shut up with his 'Let's take college seriously' campaign for the rest of the school year.

He sincerely hoped that Caroline was too smart to be seduced by Kol.

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A.N.:

Thank you appreciation, nicaha23, LiveLaughDreamInspire, drewwnesss, butterflymm19, scarletmoon66, peachx89, iwannabemrsfelton, Hi and the three guest reviewers who reviewed Chapter 1! I am so glad that I'm not the only person who thinks that this couple is great.

I hope you weren't put off by Kol's cockiness (he'll mellow eventually, don't worry) and the temporary lack of Kolaroline. I'm planning major Kolaroline moments for next chapter so please review to let me know that you still like this story and that I should go on.


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